CN109863200B - 低聚酯组合物及其制备和使用方法 - Google Patents
低聚酯组合物及其制备和使用方法 Download PDFInfo
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- CN109863200B CN109863200B CN201780065467.6A CN201780065467A CN109863200B CN 109863200 B CN109863200 B CN 109863200B CN 201780065467 A CN201780065467 A CN 201780065467A CN 109863200 B CN109863200 B CN 109863200B
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F1/00—Obtaining purification, or chemical modification of natural resins, e.g. oleo-resins
- C09F1/04—Chemical modification, e.g. esterification
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L93/00—Compositions of natural resins; Compositions of derivatives thereof
- C08L93/04—Rosin
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D193/00—Coating compositions based on natural resins; Coating compositions based on derivatives thereof
- C09D193/04—Rosin
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/004—Reflecting paints; Signal paints
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J193/00—Adhesives based on natural resins; Adhesives based on derivatives thereof
- C09J193/04—Rosin
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J201/00—Adhesives based on unspecified macromolecular compounds
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US201662398723P | 2016-09-23 | 2016-09-23 | |
US62/398,723 | 2016-09-23 | ||
PCT/US2017/053126 WO2018058005A1 (fr) | 2016-09-23 | 2017-09-23 | Compositions d'oligoesters et procédés de fabrication et d'utilisation associés |
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CN109863200A CN109863200A (zh) | 2019-06-07 |
CN109863200B true CN109863200B (zh) | 2022-01-18 |
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US (1) | US10407593B2 (fr) |
EP (1) | EP3504267B8 (fr) |
JP (1) | JP7112390B2 (fr) |
CN (1) | CN109863200B (fr) |
WO (1) | WO2018058005A1 (fr) |
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CN115386397B (zh) * | 2021-05-19 | 2024-06-04 | 国家能源投资集团有限责任公司 | 精制蜡、费托粗蜡的精制方法和系统 |
CN113388327A (zh) * | 2021-07-13 | 2021-09-14 | 桂林兴松林化有限责任公司 | 一种胶类产品加工助剂的松香甘油酯生产工艺 |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63301969A (ja) * | 1987-06-02 | 1988-12-08 | Ricoh Co Ltd | 静電荷像現像用液体現像剤 |
WO1995002019A3 (fr) * | 1993-07-09 | 1995-01-19 | Dsm Nv | Resine alkyde sechant a l'air et emulsion la comportant |
CN1400994A (zh) * | 2000-02-17 | 2003-03-05 | 阿克佐诺贝尔公司 | 聚酯增粘剂及粘合剂组合物 |
EP2012185A1 (fr) * | 2006-04-21 | 2009-01-07 | Kao Corporation | Polyester for toner |
CN103492953A (zh) * | 2011-03-29 | 2014-01-01 | 夏普株式会社 | 调色剂及其制造方法 |
CN104610536A (zh) * | 2013-11-05 | 2015-05-13 | 富士施乐株式会社 | 聚酯树脂、静电荷图像显影用调色剂、以及调色剂容器 |
CN105722910A (zh) * | 2013-09-27 | 2016-06-29 | 阿利桑那化学公司 | 包含乙烯聚合物的组合物 |
CN108699395A (zh) * | 2015-12-31 | 2018-10-23 | 科腾化学品有限责任公司 | 低聚酯及其组合物 |
Family Cites Families (52)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB599546A (en) | 1943-08-17 | 1948-03-16 | Hercules Powder Co Ltd | Improvements in or relating to coating compositions |
US1820265A (en) | 1928-11-24 | 1931-08-25 | Hercules Powder Co Ltd | Ester gum and method of producing |
US2017866A (en) | 1930-05-03 | 1935-10-22 | Columbia Naval Stores Company | Process for improving rosin |
US2108928A (en) | 1936-02-08 | 1938-02-22 | Hercules Powder Co Ltd | Method for the polymerization of rosin |
US2181054A (en) | 1936-08-21 | 1939-11-21 | Modified alkyd resin | |
US2369125A (en) | 1941-06-28 | 1945-02-13 | Hercules Powder Co Ltd | Rosin esters and method of producing |
GB563554A (en) | 1941-11-12 | 1944-08-21 | Hercules Powder Co Ltd | Improvements in or relating to alkyd resins and their method of preparation |
US2518497A (en) | 1946-03-15 | 1950-08-15 | Montclair Res Corp | Unsaturated fatty acid modified rosin esters and process of preparing same |
GB680996A (en) | 1948-03-02 | 1952-10-15 | Herbert Hoenel | Modified alkyd resins |
GB729424A (en) | 1951-01-18 | 1955-05-04 | Lewis Berger & Sons Ltd | Improvements in or relating to oil-soluble polymeric compounds |
US2791568A (en) | 1952-02-02 | 1957-05-07 | Armour & Co | Non-yellowing baking finish |
US2729660A (en) | 1953-01-21 | 1956-01-03 | Gen Mills Inc | Phosphite esters as esterification catalysts |
US2889293A (en) | 1956-04-02 | 1959-06-02 | American Cyanamid Co | Mixture of certain oil-modified alkyd resins blended with a resinous reaction product of certain acids with an adduct of an alkylene oxide with certain polyhydric alcohols |
US2965588A (en) | 1958-04-11 | 1960-12-20 | American Cyanamid Co | Mixture of an oil modified alkyd composition, a polyacrylamide, and a resinous reaction product of an alkylene oxide adduct with a polyhydric alcohol |
BE628693A (fr) | 1961-04-14 | |||
BE646253A (fr) | 1964-01-28 | 1964-07-31 | ||
US3423389A (en) | 1967-10-05 | 1969-01-21 | Arizona Chem | Rosin compounds of improved color and stability |
US3780013A (en) | 1972-12-18 | 1973-12-18 | Arizona Chem | Preparation of color improved tall oil rosin pentaerythritol esters |
JPS5249811B2 (fr) * | 1973-08-28 | 1977-12-20 | ||
US3959410A (en) | 1974-08-12 | 1976-05-25 | The Goodyear Tire & Rubber Company | Butadiene grafted ethylene-vinyl acetate hot melt adhesive |
US4100119A (en) | 1975-10-20 | 1978-07-11 | Standard Oil Company (Indiana) | Greater water resistance and shorter drying time in water soluble enamel paints |
US4172070A (en) | 1978-03-27 | 1979-10-23 | Arizona Chemical Company | Oxygen-stable rosin-primary polyhydric aliphatic alcohol esters and a method for preparing the same utilizing arylsulfonic acid catalysis |
JPS559605A (en) | 1978-06-23 | 1980-01-23 | Arakawa Chem Ind Co Ltd | Preparation of rosin ester having high softening point and improved stability |
US4368316A (en) | 1980-06-02 | 1983-01-11 | Sun Chemical Corporation | Process for the preparation of high-solids rosin-modified polyesters |
US4377510A (en) | 1981-11-30 | 1983-03-22 | Arizona Chemical Company | Urethane-modified rosin ester and process for preparing the same |
US4380513A (en) | 1981-11-30 | 1983-04-19 | Arizona Chemical Company | Inert rosin esters and process for preparing the same |
DE3244399A1 (de) | 1982-12-01 | 1984-06-07 | Rentrop Hubbert & Wagner | Gelenkbeschlag fuer kraftfahrzeugsitze mit verstellbarer lehne |
US4548746A (en) | 1984-05-14 | 1985-10-22 | Westvaco Corporation | Rosin pentaerythritol ester preparation improvement |
US4650607A (en) | 1985-05-09 | 1987-03-17 | Westvaco Corporation | Method for rosin esterification |
US4657703A (en) | 1986-06-30 | 1987-04-14 | Hercules Incorporated | Method of improving the color of tall oil rosin esters |
US4690783A (en) | 1986-08-29 | 1987-09-01 | Union Camp Corporation | Method of preparing rosin ester from polyol with phosphorous acid catalyst |
US4788009A (en) | 1986-11-14 | 1988-11-29 | Union Camp Corporation | Method of preparing rosin esters of improved thermal stability with inorganic salt of phosphorous or hypophosphorous acid |
US4693847A (en) | 1986-11-14 | 1987-09-15 | Union Camp Corporation | Method of preparing hot-melt stable rosin ester with organic ester of hypophosphorous acid catalyst |
US4725384A (en) | 1986-11-17 | 1988-02-16 | Westvaco Corporation | Method for rosin esterification in the presence of phosphinic acid and phenol sulfide and subsequent neutralization with a magnesium salt |
JPS6428656A (en) * | 1987-07-23 | 1989-01-31 | Nippon Synthetic Chem Ind | Binder resin for toner |
US5021548A (en) | 1990-01-22 | 1991-06-04 | Hercules Incorporated | Sodium hydroxymethane sulfonate to improve the color stability of rosin resins |
US5036129A (en) | 1990-04-17 | 1991-07-30 | Great Lakes Chemical Corporation | Flame retardant hot melt adhesive compositions |
US5049652A (en) | 1990-11-30 | 1991-09-17 | Hercules Incorporated | Use of a mixed catalyst system to improve the viscosity stability of rosin resins |
US5120781A (en) | 1991-05-07 | 1992-06-09 | Union Camp Corporation | Acid-modified polyhydric alcohol rosin ester tackifiers and hot melt adhesive compositions containing those tackifiers |
US5504152A (en) | 1995-01-10 | 1996-04-02 | Arizona Chemical Company | Esterification of rosin |
AU5733200A (en) | 1999-06-11 | 2001-01-02 | Eastman Chemical Resins, Inc. | Polyols, polyurethane systems and polyurethane reactive hot melt adhesives produced thereon |
US20110034669A1 (en) | 2006-02-02 | 2011-02-10 | Dallavia Anthony J | Rosin Ester with Low Color and Process for Preparing Same |
US8459319B2 (en) * | 2009-08-31 | 2013-06-11 | The Goodyear Tire & Rubber Company | Tire with rubber tread containing combination of resin blend and functionalized elastomer |
US9499709B2 (en) * | 2010-03-01 | 2016-11-22 | Xerox Corporation | Oligomeric rosin esters for use in inks |
JP5710320B2 (ja) * | 2010-03-31 | 2015-04-30 | 富士フイルム株式会社 | デヒドロアビエチン酸由来の重合体およびその用途 |
FR2965267B1 (fr) | 2010-09-27 | 2013-11-15 | Cray Valley Sa | Resines polyesters a base d'acides gras de longueur en huile courte, dispersions aqueuses et revetements lies |
EP2640791B1 (fr) | 2010-11-19 | 2020-04-22 | Henkel IP & Holding GmbH | Compositions adhésives et leurs utilisations |
EP2847248B1 (fr) | 2012-05-08 | 2016-07-13 | DSM IP Assets B.V. | Résine, composition et utilisation |
EP2972350A4 (fr) * | 2013-03-14 | 2016-11-23 | Church & Dwight Co Inc | Dispositif de test de diagnostic à affichage amélioré |
FR3009304B1 (fr) | 2013-08-05 | 2016-09-30 | A Et A Mader | Resine alkyde biosourcee et procede de fabrication d'unte telle resine alkyde |
KR102464692B1 (ko) | 2015-03-26 | 2022-11-09 | 크라톤 케미칼, 엘엘씨 | 로진 에스테르와 에틸렌 중합체를 포함하는 조성물 |
JP6428656B2 (ja) | 2016-01-16 | 2018-11-28 | 三菱ケミカル株式会社 | 積層ポリエステルフィルム |
-
2017
- 2017-09-23 WO PCT/US2017/053126 patent/WO2018058005A1/fr unknown
- 2017-09-23 CN CN201780065467.6A patent/CN109863200B/zh active Active
- 2017-09-23 US US15/713,644 patent/US10407593B2/en active Active
- 2017-09-23 EP EP17854053.0A patent/EP3504267B8/fr active Active
- 2017-09-23 JP JP2019516225A patent/JP7112390B2/ja active Active
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63301969A (ja) * | 1987-06-02 | 1988-12-08 | Ricoh Co Ltd | 静電荷像現像用液体現像剤 |
WO1995002019A3 (fr) * | 1993-07-09 | 1995-01-19 | Dsm Nv | Resine alkyde sechant a l'air et emulsion la comportant |
CN1400994A (zh) * | 2000-02-17 | 2003-03-05 | 阿克佐诺贝尔公司 | 聚酯增粘剂及粘合剂组合物 |
EP2012185A1 (fr) * | 2006-04-21 | 2009-01-07 | Kao Corporation | Polyester for toner |
CN103492953A (zh) * | 2011-03-29 | 2014-01-01 | 夏普株式会社 | 调色剂及其制造方法 |
CN105722910A (zh) * | 2013-09-27 | 2016-06-29 | 阿利桑那化学公司 | 包含乙烯聚合物的组合物 |
CN104610536A (zh) * | 2013-11-05 | 2015-05-13 | 富士施乐株式会社 | 聚酯树脂、静电荷图像显影用调色剂、以及调色剂容器 |
CN108699395A (zh) * | 2015-12-31 | 2018-10-23 | 科腾化学品有限责任公司 | 低聚酯及其组合物 |
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WO2018058005A1 (fr) | 2018-03-29 |
EP3504267A4 (fr) | 2020-05-06 |
CN109863200A (zh) | 2019-06-07 |
EP3504267B1 (fr) | 2024-08-21 |
EP3504267B8 (fr) | 2024-10-16 |
US10407593B2 (en) | 2019-09-10 |
EP3504267C0 (fr) | 2024-08-21 |
EP3504267A1 (fr) | 2019-07-03 |
US20180086942A1 (en) | 2018-03-29 |
JP2020500949A (ja) | 2020-01-16 |
JP7112390B2 (ja) | 2022-08-03 |
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